Novel molecular receptors based on a thiacalix[4]arene platform. Preparations of the di- and tetracarboxylic acid derivatives and their binding properties towards transition metal ions

Tetrahedron Letters

Volumn 40, Issue 41, 1999, Pages 7337-7341

  Nobuhiko, Iki ^a   Morohashi, Naoya ^a   Narumi, Fumitaka ^a   Fujimoto, Toyohisa ^a   Suzuki, Tomohiro ^a   Miyano, Sotaro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Alkylation; Calixarenes; Complexation; Sulfides

Indexed keywords

CALIXARENE; CARBOXYLIC ACID; METAL ION; SULFIDE;

ALKYLATION; ARTICLE; COMPLEX FORMATION; METAL BINDING; REACTION ANALYSIS; SYNTHESIS;

EID: 0033536654     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01503-8     Document Type: Article

References (18)

1. 1. Kumagai, H.; Hasegawa, M.; Miyanari, S.; Sugawa, Y.; Sato, Y.; Hori, T.; Ueda, S.; Kamiyama, H.; Miyano, S. Tetrahedron Lett. 1997; 38, 3971-3972.
2. 2. Iki, N.; Morohashi, N.; Narumi, F.; Miyano, S. Bull. Chem. Soc. Jpn. 1998, 71, 1597-1603.
3. 3. Iki, N.; Morohashi, N.; Kabuto, C.; Miyano, S. Chem. Lett. 1999, 219-220.
4. 4. Iki, N.; Narumi, F.; Fujimoto, T.; Morohashi, N.; Miyano, S. J. Chem. Soc., Perkin Trans. 2 1998, 2745-2750.
5. 5. Iki, N.; Fujimoto, T.; Miyano, S. Chem. Lett. 1998, 625-626.
6. 6. Iki, N.; Narumi, F.; Suzuki, T.; Sugawara, A.; Miyano, S. Chem. Lett. 1998, 1065-1066.
7. 7. Narumi, F.; Iki, N.; Suzuki, T.; Onodera, T.; Miyano, S. Enantiomer, in press.
8. 8. Recently, the same results were reported by another group. See: Akdas, H.; Mislin, G.; Graf, E.; Hosseini, M. W.; Cian, A. D.; Fischer, J. Tetrahedron Lett. 1999, 40, 2113-2116.
9. 4: C, 64.56; H, 6.77; S, 14.36. Found: C, 64.62; H, 6.90; S, 14.05.
10. 10. Although syn-6 may have cone or 1,3-alternate conformation, the conformation of syn-4 could not be assigned to a particular one because of the 'oxygen-through-the-annulus rotation'.
11. 11. Ogata, M.; Fujimoto, K.; Shinkai, S. J. Am. Chem. Soc. 1994, 116, 4505-4506.
12. 12. See also: Iwamoto, K.; Yanagi, A.; Araki, K.; Shinkai, S. Chem. Lett. 1991, 473-476.
13. 13. Araki, K.; Iwamoto, K.; Shinkai, S.; Matsuda, T. Chem. Lett. 1989, 1747-1750.
14. 4: C, 63.13; H, 6.26; S, 15.32. Found: C, 63.02; H, 6.00; S, 15.33.
15. aq,init×100%.
16. 16. The cone conformer of 9 was prepared by the same fashion as in Ref. 14.
17. 2
18. 3+, E% values could not be obtained due to the formation of precipitation.